3-oxa-16-pentacosenamide and 3-oxa-12-heneicosenamide



United States Patent 3,467,706 3-OXA-16-PENTACOSENAMIDE AND 3-OXA-12- HENEICOSENAMIDE I Robert W. Hill, Leawood, and Thomas R. Hopkins, Over- US. Cl. 260-561 2 Claims ABSTRACT OF THE DISCLOSURE New compounds 3-oxa-l6-pentacosenamide and 3-oxa- 12-heneicosenamide, which are useful as slip agents for olefin polymers.

This invention relates to novel amides, methods for preparing same, and olefin poymer compositions containing same.

In the manufacture of olefin polymer films such as polyethylene film and polypropylene film, it is customary to incorporate into the polymer a material which blooms to the surface of the film and functions as a lubricant. Such materials are referred to in the art as slip agents. Although a wide variety of materials have been proposed for use as slip agents in olefin polymers, only two compounds are widely used for this purpose, viz., oleamide and erucamide. Olefin polymer compositions containing oleamide and/or erucamide as a slip agent are subject to a number of known shortcomings. First, film manufactured from such compositions frequently has an undesirable odor. Second, these slip agents frequently exude from the polymer at an extremely rapid rate and/or are volatilized from the polymer and deposit on surfaces which come into contact with the film. This is particularly the case when the polymer is extruded by a chill roll casting method or by a blown film method in which internal formers or mandrels are employed. The deposition of the slip agent on such surfaces which come into contact with the film frequently will cause imperfections in the film. Third, the rapid exudation of these amides to the surface of the film frequently overlubricates the film surface so that it is difficult to wind the film tightly upon a core. This phenomenon is sometimes referred to as telescoping.

It is an object of this invention to provide novel compounds which are useful as slip agents in olefin polymers, particularly polyethylene and polypropylene.

Another object of this invention is to provide processes for preparing novel compounds which are useful as slip agents in olefin polymers.

A further object of the invention is to provide olefin polymer compositions containing therein novel slip agents.

A still further object of the invention is to provide olefin polymer films containing therein novel slip agents, which films are characterized by having a low coeflicient of friction (i.e. high slip), good resistance to blocking and good printability.

Yet another object of the invention is to provide an improved method for chill roll casting olefin polymer films in which novel slip agents are included in the olefin polymer being extruded.

The above and related objects are attained by preparing amides of the formula:

where X is 8 or 12. Such amides can be prepared by synthesis methods subsequently described. Such amides,

3,467,706 Patented Sept. 16, 1969 when incorporated into olefin polymer films, function as an extremely eflicient slip agent to provide olefin polymer films having a desirable combination of characteristics not heretofor available to the art. Particularly valuable properties are obtained when the olefin polymer compositions of this invention are converted into film by a chill roll casting method.

The following examples are set forth to illustrate more clearly the principle and practice of this invention to those skilled in the art. \Except Where otherwise noted, where parts or percentages are set forth, they are parts or percentages by weight.

EXAMPLE I =Part A Incorporate 0.1% of 3-oxa-12-heneicosenamide into a film grade polyethylene resin having a density of 0.92 and a melt index of 2 by banburying the materials for 10 minutes at a temperature of about F. in a laboratory-size Banbury mixer. Sheet the resulting polymer composition on a mill roll and comminute to a particle size suitable for extrusion.

Part B Convert the polymer composition prepared in Part A into film by extruding the composition in a 2" laboratory extruder equipped with a 4" diameter tubular film die. Extrude at a die temperature of 375 F. and inflate the bubble to form a 10" wide tubular film lay-flat. The film thickness will be approximately one mil. The film thus prepared will have a coefficient of friction of about 0.14 as measured by the standard ASTM Test Method. The film, when treated with a corona discharge, will be readily printable with inks conventionally used in the polyethylene film converting industry.

EXAMPLE 11 Part A Incorporate 0.05% of 3-oXa-16-pentacose1ramide into a film grade polyethylene resin having a density of about 0.935 and a melt index of about 2 following the procedure of Example I, Part A.

Part B Extrude the composition of Part A into film employing laboratory scale conventional chill roll casting equipment where X is 8 or 12. The amides embraced by the formula are, respectively:

3-oxa-16-pentacosenamide 3-oxa-12-heneicosenamide By reason of the double bond, the amides can exist in either the cis or trans isomer form. The cis isomer forms are presently preferred for use as slip agents in olefin polymers. The most preferred isomer for the purpose of the present invention is cis-4-oxa-lfi-pentacosenamide.

4-oxa-16-pentacosenamide can be prepared directly by reacting the sodium salt of l3-docosen-1-ol(erucyl alcocho1a known compound) with chloroacetamide. Al-

ternatively, the sodium salt of the 13-docosen-1-ol can be reacted with sodium chloroacetate to prepare 4-oxa-16- pentacosenoic acid which dan be reacted with ammonia to give the desired 4-oxa-l-pentacosenamide. Other classical methods for preparing the 4-oxa-16-pentacosenamide will be apparent to those skilled in the art. 3-oxa-l2-heneicosenamide can be prepared by aualagous reactions except that 9-octadecen-1-ol (oleyl alcohol) will be used as the starting material in lieu of 13-docosen-1-ol.

The olefin polymer compositions of this invention can be prepared by incorporating the amides into the olefin polymer by compounding methods well-known in the art. The amides will be used in the amount of about 0.005-l.0% 'and preferably 0.025-0.1% by weight of the olefin polymer.

The olefin polymers that can be used in preparing the olefin polyuner compositions of this invention are any of the common polymers of mono-olefins used for fabrication into film. Such polymers include ethylene copolymers, propylene copolymers and preferably polyethylene and polypropylene.

The olefin polymer compositions of the invention can be converted into film by any of the fabrication techniques currently employed in the film-making art. These methods include the Well-known blown film extrusion 4 technique and the chill roll casting technique. The polymer compositions of the invention are particularly useful in manufacturing film by the chill roll casting technique in which the polymer is extruded at a die temperature of at least about 500 F.

It has been observed that higher than conventional extrusion temperatures can be used without encountering the difiiculties normally associated with the loss of the slip agent through volatilization. The use of higher temperatures enables the film manufacturer to extrude at higher temperatures and thereby obtain higher rates of production and concomitantly lower manufacturing costs.

What is claimed is:

1. 3-oxa-16-pentacosenamide.

2. 3-oXa-l2-heneicosenamide.

No references cited.

ALEX MAZEL, Primary Examiner J. A. NARCAVAGE, Assistant Examiner U.S. Cl. X.R. 

